Meclinertant

Base Information

• Chemical Name: Meclinertant
• CAS No.: 146362-70-1
• Molecular Formula: C32H31 Cl N4 O5
• Molecular Weight: 587.075
• UNII: 5JBP4SI96H
• DSSTox Substance ID: DTXSID40163360
• Nikkaji Number: J567.748C
• Wikipedia: Meclinertant
• Wikidata: Q7392763
• NCI Thesaurus Code: C156766
• Pharos Ligand ID: CC79Q36W1NW8
• Metabolomics Workbench ID: 149788
• ChEMBL ID: CHEMBL506981
• Mol file: 146362-70-1.mol

Synonyms:2-((1-(7-chloro-4-quinolinyl)-5-(2,6-dimethoxyphenyl)pyrazol-3-yl)carbonylamino)tricyclo(3.3.1.1.(3.7))decan-2-carboxylic acid;Meclinertant;SR 48692;SR-48692;SR48692

Chemical Property of Meclinertant

Chemical Property:

• Vapor Pressure: 1.08E-25mmHg at 25°C
• Boiling Point: 781.2°C at 760 mmHg
• Flash Point: 426.2°C
• PSA: 119.06000
• Density: 1.5g/cm³
• LogP: 6.34220
• Storage Temp.: ?20°C
• Solubility.: DMSO: ≥2mg/mL (warmed)
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 586.1982978
• Heavy Atom Count: 42
• Complexity: 991

Purity/Quality:

98%,99%, ^*data from raw suppliers

SR 48692 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=CC=C1)OC)C2=CC(=NN2C3=C4C=CC(=CC4=NC=C3)Cl)C(=O)NC5(C6CC7CC(C6)CC5C7)C(=O)O
• Recent ClinicalTrials: Evaluation of the Overall Survival of Meclinertant Versus Placebo After a First Line Chemotherapy With Cisplatin + Etoposide
• Uses: SR 48692 has been used as a neurotensin?high-affinity receptor 1 (NTSR1) antagonist: to explore the function of NTSR1 in glioblastoma (GBM) cells to determine the roles of neurotensin (NT) in the regulation of bile acid?(BA) uptake, in vivo to explore the involvement of NTSR1 versus NTSR2 in mice

Technology Process of Meclinertant

There total 14 articles about Meclinertant which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

tert-butyl 2-[1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxamido]adamantane-2-carboxylate (1443991-23-8) → merclinertant (146362-70-1)

Guidance literature:

With QP-SA; In dichloromethane; at 18 ℃; for 20h;

DOI:10.1002/chem.201300696

Reference yield:

ethyl 1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylate (1443991-22-7) → merclinertant (146362-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium hydroxide / water; tetrahydrofuran / 2 h / 120 °C / Microwave irradiation

2: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine; bis(trichloromethyl) carbonate / dichloromethane / 18 h / 20 °C

3: QP-SA / dichloromethane / 20 h / 18 °C

With 2,6-dimethylpyridine; bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/chem.201300696

Reference yield:

2,6-dimethoxyacetophenone (2040-04-2) → merclinertant (146362-70-1)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium ethanolate / ethanol / 0.42 h / 80 °C / Microwave irradiation

2: N,N-dimethyl-formamide / 3 h / 140 °C / Microwave irradiation

3: potassium hydroxide / water; tetrahydrofuran / 2 h / 120 °C / Microwave irradiation

4: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine; bis(trichloromethyl) carbonate / dichloromethane / 18 h / 20 °C

5: QP-SA / dichloromethane / 20 h / 18 °C

With 2,6-dimethylpyridine; bis(trichloromethyl) carbonate; sodium ethanolate; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 1: |Claisen Condensation;

DOI:10.1002/chem.201300696

upstream raw materials:

ethyl 1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylate

2-amino-2-adamantanecarboxylic acid

tert-butyl 2-[1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxamido]adamantane-2-carboxylate

2'-hydroxy-6'-methoxyacetophenone

Refernces

• 1、 Baxendale,Cheung,Kitching,Ley,Shearman. "The synthesis of neurotensin antagonist SR 48692 for prostate cancer research". . p. 4378 - 4387. Retrieved 2013/07/27.